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【结 构 式】

【分子编号】15972

【品名】3-(1-acetyl-4-piperidinyl)-1-(1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone

【CA登记号】

【 分 子 式 】C22H30N2O3

【 分 子 量 】370.49188

【元素组成】C 71.32% H 8.16% N 7.56% O 12.96%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

The Friedel-Crafts condensation of 1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepine (I) with 3-(1-acetylpiperidin-4-yl)propionyl chloride (II) by means of AlCl3 in 1,2-dichloroethane gives 3-(1-acetylpiperidin-4-yl)-1-(1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone (III), which is deacetylated in refluxing concentrated aqueous HCl yielding 3-(piperidin-4-yl)-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone (IV). Finally, this compound is benzylated with benzyl bromide (V) and K2CO3 in ethanol affording the final product as free base, which is then treated with fumaric acid in MeOH/CH2Cl2.

1 Mealy, N.; Rabasseda, X.; Castaner, J.; TAK-147. Drugs Fut 1995, 20, 3, 248.
2 Goto, G.; Ishihara, Y.; Miyamoto, M. (Takeda Chemical Industries, Ltd.); Condensed heterocyclic cpds., their production and use. EP 0487071; US 5273974 .
3 Ishihara, Y.; Hirai, K.; Miyamoto, M.; Goto, G.; Central cholinergic agents. 6. Synthesis and evaluation of 3-[1-(phenylmethyl)-4-piperidinyl]-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanones and their analogs as central selective acetylcholinesterase inhibitors. J Med Chem 1994, 37, 15, 2292-9.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 15970 1-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)-1-ethanone C12H15NO 详情 详情
(II) 15971 3-(1-acetyl-4-piperidinyl)propanoyl chloride C10H16ClNO2 详情 详情
(III) 15972 3-(1-acetyl-4-piperidinyl)-1-(1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone C22H30N2O3 详情 详情
(IV) 15973 3-(4-piperidinyl)-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)-1-propanone C18H26N2O 详情 详情
(V) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
Extended Information